71159-33-6Relevant articles and documents
A new mechanism of enantioselectivity toward chiral primary alcohol by lipase from Pseudomonas cepacia
Meng, Xiao,Guo, Li,Xu, Gang,Wu, Jian-Ping,Yang, Li-Rong
, p. 109 - 115 (2014/12/11)
The stereo-recognition of chiral primary alcohols by lipase from Pseudomonas cepacia was found to deviate from earlier observations. Enantioselectivity toward 14 pairs of chiral primary alcohol esters by this lipase was dependent on the existence of an Onon-α(oxygen at non-α-position of the acyloxy group) in the alcohol moiety, and decreased as the size of the acyl moiety increased. Chemical modification on the lipase and molecular dynamics simulations indicated that Tyr29located within the catalytic cavity forms a hydrogen bond with the Onon-αof the preferred enantiomer of the primary alcohol ester. However, a larger acyl moiety suffered stronger hindrance from the catalytic cavity wall of the lipase, pushing the Onon-αaway from Tyr29, and thus weakening the stereo-recognition.
Resolution of 2-aryloxy-1-propanols via lipase-catalyzed enantioselective acylation in organic media
Miyazawa, Toshifumi,Yukawa, Tomoyuki,Koshiba, Takashi,Sakamoto, Hiroko,Ueji, Shinichi,Yanagihara, Ryoji,Yamada, Takashi
, p. 1595 - 1602 (2007/10/03)
2-Aryloxy-1-propanols, primary alcohols with an oxygen atom at the stereocenter, were resolved with good to high enantioselectivity by acylation with vinyl butanoate mediated by Pseudomonas sp. lipase in di-iso-propyl ether. Potential factors affecting the enantioselectivity of the enzymatic acylation were examined: solvents, acyl donors and temperature. Using this enantioselective acylation procedure, enantiomerically pure (R)-2-(4-chlorophenoxy)-1-propanol was prepared on a gram scale.